IOWA STUBBORN: Mayor de Blasio has yet to make the leap from fractions to whole numbers in the Democratic presidential polls and there are problems and issues in New York that would seem to demand his attention, but he kept tramping through the cornfields and roads of Iowa, from Des Moines to Blanchard, trying to drum up support for his candidacy, because he found it a sunnier climate than back home.

De Blasio's Neverland: A Long, Strange Trip

IOWA STUBBORN: Mayor de Blasio has yet to make the leap from fractions to whole numbers in the Democratic presidential polls and there are problems and issues in New York that would seem to demand his attention, but he kept tramping through the cornfields and roads of Iowa, from Des Moines to Blanchard, trying to drum up support for his candidacy, because he found it a sunnier climate than back home.

In March 2018, I was asked by a higher-up on the Inner Circle script committee to write the show’s opening number, focusing on Mayor de Blasio to the tune of the song that opened “The Producers.”

The original song’s title, “The Worst Show in Town,” was a tipoff that I should not construct what another Broadway musical called “A Hymn to Him.” And so the lyric was divided between Mr. de Blasio’s recent re-election and indications he had already given that he would launch a campaign for President and featured the couplet, “Let him run and we’ll stand up and cheer/Life is better when he’s not here.”

Judging by New Yorkers’ reaction to his actual campaign, that sentiment has currency beyond the laughs it generated in our show. Yet many of those who would endorse that line are also resentful that the Mayor is spending so much time on the campaign trail and so little, it seems, doing the job for which he will be paid for the next 28 months.

Unless, of course, he wins the White House and is forced to step down as Mayor in January 2021. Yeah, I know: that’s a laugh.

Deep-Fried But Not Popping

This may account for the ambivalence mixed with outrage about his quixotic campaign. Mr. de Blasio recently spent an inordinate amount of time in Iowa along with 20 or so other Democrats driving up their cholesterol counts in hopes of lining up support for next year’s caucuses that mark the first voting that party members will do toward choosing their nominee. He has not exactly caught fire in the Hawkeye State: the New York Post, having a merry time describing his futility on the trail, reported that the traditional corn-kernel poll at the Iowa State Fair had garnered him just 25 kernels out of more than 20,000 cast.

That is consistent with the Mayor’s national standing. He has failed to reach 1 percent in national polls, and unless he can get to 2 percent in at least four polls by Aug. 28, he won’t be included in the next round of party debates in Houston Sept. 12 and 13. Which would mean his best shot at exposure, at a point when the tougher standards now taking effect will thin out the herd enough to offer candidates who qualify more time to speak, would be lost.

The Mayor downplayed that possibility during his Aug. 12 appearance on “Inside City Hall,” telling host Errol Louis that “debates are a fantastic opportunity to speak to, you know, 20 million or more people, but they are also a flawed dynamic by definition. You know, at this point we’ve had 10 people on a stage and a format that only allows so much give and take.”

It wasn’t the limits of the format, however, that triggered Mr. de Blasio’s decision during the July 31 debate to make an issue of the 800,000 deportations ordered by President Obama or the Justice Department’s inability during the last two years of his tenure to decide whether to bring a civil-rights case against Daniel Pantaleo, both areas where he sought to hold ex-Vice President Joe Biden accountable. The irony was that, in the latter case, the Mayor himself could have exerted far more pressure than Mr. Biden to speed action on the Eric Garner case, and instead allowed his Police Commissioners to delay an internal disciplinary hearing against Officer Pantaleo until nearly five years after the fatal confrontation.

His willingness to light into Mr. Obama on those issues, and question the effectiveness of his health-care plan by making a case for scrapping it in favor of Medicare for All, seemed to dispel thoughts that Mr. de Blasio was using the campaign as an audition for a top post in the national Democratic Party. His low standing in the polls would seem to eliminate the possibility of his being a stronger candidate’s idea of a running mate, particularly given that New York is not exactly a battleground state in next year’s election.

And so the man who when not chowing down on Midwest delicacies like a sugar-grilled pork belly on a stick drinks his morning beverage in a Park Slope patisserie was practically crying out for psychoanalysis regarding his unwillingness to smell the espresso and ride off the campaign trail and back to his day job.

Downplays Debates

He told Mr. Louis, “I would argue, the second-toughest job in America, as it has often been called [most frequently by New York City Mayors and their image-shapers], is something that immediately qualifies you as someone for consideration and people should want to hear, you know, what I’ve done in six years as Mayor of this city and what my vision is, because I’ve already done something substantial…but when you really get out of the first days after the debates, the big strokes of this election so far, six months, seven months, have not been based on the debate performances. They just haven’t.”

“That’s right,” Mr. Louis replied.

“So that’s where I’m not gonna overrate it,” Mr. de Blasio said. “I’m going to make my decisions about what I’m going to do based on the whole picture.”

What his analysis ignored was that while Joe Biden bounced back from a dreadful opening-debate performance that hurt but didn’t cripple him in the polls, and Kamala Harris soared in their first encounter but fell back to earth in the second, each had previously carved out spots in the top tier, rather than being stuck, as Mr. de Blasio was, among candidates who hadn’t broken into whole numbers in the polls and weren’t admitted to the earlier debates.

When Mr. Louis asked whether his big-picture strategy meant he would continue campaigning even if he was excluded from the debates, the Mayor replied, “Yeah, I would absolutely say that. I’m going to look at all the pieces and look, again, six months until anyone votes, you know, that’s what we have to keep in mind.”

Which would get him to the Iowa caucuses, and maybe then to New Hampshire. And once he’s stayed in that long, why not hang in until the New York primary April 28? A bigger question might be whether the Police Benevolent Association, which continues to follow Mr. de Blasio along the presidential trail because, as a spokesman reiterated last week, “We want people to know the truth: he’s no friend of labor or of working people,” will keep spending the money on a traveling jeering section.

A Shaker, Not a Mover

There is no question the Mayor revels in the give-and-take of the campaign, since it allows him to talk about big issues and left-wing politics—one local critic, John Jay College Professor Gene O’Donnell, earlier this month said he was “channeling the Democratic Socialists of America at City Hall.” For Mr. de Blasio, that beats having to respond to the New York media’s questions about an ethical compass that allows him to say with a straight face, regarding a Daily News report that members of his security detail had helped his daughter Chiara move her worldly possessions from a Brooklyn apartment to Gracie Mansion, that he wasn’t present when it happened so he couldn’t comment.

He gives the impression that he likes the perks and prestige of being Mayor, but when it comes to accountability would prefer being in his old role as Public Advocate, when he could critique the universe and not have to explain why his administration falsified reports on lead contamination in Housing Authority apartments and fudged the numbers on how many small children may have had their health compromised as a result.

He still rolls out his greatest-hits compilation from his Public Advocate days. In an Aug. 2 press conference after the NYPD’s Deputy Commissioner of Trials recommended that Mr. Pantaleo be fired for using a department-banned chokehold to subdue Mr. Garner, the Mayor invoked three highly charged cases involving cops’ use of force against unarmed black men: Abner Louima, Amadou Diallo and Sean Bell.

Seven years ago, after a speech on criminal justice covering those cases at John Jay that was an early foray into the mayoral race, he was asked about an important distinction separating the Bell case from the other two. Sean Bell had played a pivotal role in the events that led to his being fatally shot by police, first by getting into a loud confrontation with a man who pantomimed brandishing a gun outside a notorious Queens club, then walking off with a friend who vowed to get a gun of his own, prompting an undercover cop to believe they were about to engage in a drive-by shooting of their antagonist. When the cop, Gescard Isnora, tried to head them off at their car, Mr. Bell drove into the officer, put the car in reverse and struck an unmarked police van, then drove toward the undercover cop again, touching off the barrage of gunfire that killed him and wounded his friend who had made the gun threat.

Mr. de Blasio conceded the point, but added that “the emotional reality of a man losing his life on the night before his wedding was very gripping.”

Misleading, Too

That didn’t justify distorting reality by linking it to the Louima and Diallo cases, where there was no question that the force used by police was excessive. And for a man who now oversees the Police Department to still be perpetuating the flawed comparison is simply irresponsible.

Kind of like running for President based on your top accomplishments at a time when the city you’re in charge of is treading water on a number of issues, most of them connected to your 2017 re-election pledge to make New York “the fairest big city in America.”

There’s the continuing mess at the HA, and Mr. de Blasio’s decision to sign off on a new Chairman who also likes to spend his weekends out of town. The city’s struggles with homelessness can be seen in the problems caused by the part of that population living in the subway system, even as no satisfactory answers have been furnished as to how more than $850 million was spent over the past four years under a mental-health-services initiative overseen by his wife and fellow campaigner, Chirlane McCray.

And for all the success of the expanded pre-kindergarten initiative that is his signature achievement, the Mayor and his two Schools Chancellors have made no headway in improving the middle schools that have long been the weak link of the city’s education system. Instead, in what amounts to misdirection, he and current Chancellor Richard Carranza have spent more than a year and significant political capital vainly trying to abolish the Specialized High School Achievement Test and impose a quota system that would increase the admission of black and Latino students at the expense of Asian ones.

The racially charged obnoxiousness of the initiative was personified when a late-July forum dealing with culturally inclusive education was held in Chinatown but no Chinese interpreters were provided—while Hispanic ones were present—until complaints were made by community activists.

‘Blamed the Translator’

Asked what explanation had been given for the lack of someone who could translate for the roughly 50 Chinese parents in the crowd who weren’t fluent in English, Amy Tse, who became a school activist in response to Mr. Carranza’s move against the SHSAT, said in an Aug. 14 phone interview, “They didn’t really have one. They blamed the translator for not showing up.”

She said she favored the topic under discussion, but when the Chancellor and his aides were asked about how adding it to the curriculum—and in a way that would include all cultures—would affect academics, “They didn’t really address that.”

Throw in a new plan circulating that would put a cap on high-achieving students in some schools, she said, and rather than lessen her mistrust of Mr. de Blasio and his Chancellor, Ms. Tse said, “It just reinforced it.”

Even the Mayor’s ability to continue reducing crime throughout his first 67 months in office has been marred by his shaky relationship with his police force.

Hasn’t Made Transition

Some of that is attributable to contract clashes with the PBA that are complicated by his need to balance that union’s interests with those of the NYPD’s other unions when it comes to compensation. But a large portion of it stems from Mr. de Blasio’s difficulty in making the transition from an activist who derived his electoral strength from his support in the black community and, to a lesser extent, the Latino one, to someone who could speak across racial lines and strike the right balance in some of the city’s most-wrenching cases.

He bungled the aftermath of a Staten Island grand jury’s dubious decision not to indict Mr. Pantaleo despite a damning videotape of his confrontation with Mr. Garner by offering an anecdote about giving his then-teenaged son “the talk” about the care with which he should handle any encounter with police. That shifted the conversation away from the mistakes made by the cops at the scene by damning the entire department as not to be trusted by people of color in tense situations.

Mr. de Blasio, who has never explicitly criticized Mr. Pantaleo and his colleagues, subsequently prejudged Sgt. Hugh Barry for fatally shooting Deborah Danner, a schizophrenic woman, after she lunged at him with a bat in her Bronx apartment in October 2016. It didn’t seem to matter to the Mayor that Mr. Barry had spent 10 minutes trying to calm Ms. Danner and persuaded her to drop a scissors that she had been brandishing before she inexplicably grabbed the bat and swung it in his direction at close range. The same “very gripping” aspects of her case that colored his view of the fatal confrontation between police and Sean Bell prompted him to harshly blame the cop less than 24 hours after the incident.

Police Commissioner James O’Neill, who had taken over the job just a month earlier, described what had occurred as a collective failure of the NYPD; the Mayor decided the Sergeant should be made the fall guy, declaring, “There are times in a huge organization when an individual does not follow their training, does not follow their instructions. The folks that had the training to handle this kind of situation were available and should’ve been deferred to.”

Those comments brushed right past the reality that the Emergency Service Unit officers who had that training weren’t actually at the scene when the confrontation unfolded, and if Ms. Danner had not abruptly seized the bat, Sergeant Barry would have been quietly celebrated for defusing a tense situation involving a woman whose mental illness left her veering between perceptive intelligence and irrational paranoia.

Further Alienated Cops

Mr. de Blasio’s condemnation of the Sergeant—who was acquitted in a criminal trial 18 months ago—further soured his relationship with rank-and-file cops. It also placed Mr. O’Neill, despite his more-measured assessment of what had occurred, in the uncomfortable position of being viewed by the officers he commanded as an accomplice in throwing Mr. Barry under the bus for using deadly force at a time when his own safety was at risk.

It’s that kind of scapegoating that has resulted in the peculiar dynamic of an administration carrying out its primary mission of continuing to reduce crime while also implementing an approach to policing aimed at promoting better relations between its officers and the communities they patrol, yet being scorned by the cops whose work lives it has been trying to make easier.

A Mayor who would seem to place more value on nuance than his recent predecessors has not earned the respect that some of his bullet-point achievements might warrant because of his difficulty communicating in pressurized, often racially-fraught situations. His empathy often seems limited to his base, where strong leaders can make themselves understood by those who don’t share their politics but will respect them for their candor. Mr. de Blasio likes the word “transcendent” but has trouble embodying it.

Discussing that flaw recently, Professor O’Donnell remarked, “He and Trump are similar people: you play with fire and you get burned…But you never satisfy extremists, so why are you trying?”

The President often seems mired in early adolescence, as if life were a rank-out contest. Mr. de Blasio appears stuck in his 20s, like the “angry young man” of Billy Joel’s song “with his fist in the air and his head in the sand/And he’s never been able to learn from mistakes/So he can’t understand why his heart always breaks.”

It was striking, watching the Mayor’s Aug. 7 appearance on Sean Hannity’s show, how relaxed he seemed in fencing with the Fox News commentator and Trump acolyte on a variety of hot-button topics.

During a discussion on gun rights, Mr. de Blasio declared, “I ain’t buyin’ what you’re sellin’…I don’t play by your rules.”

With a look on his face that brought to mind a cat playing with a mouse, he scoffed at his host’s description of him as a socialist seeking to redistribute wealth in America, saying, “I want working-class people and middle-class people to have a better life…you seem to think the status quo is ok.”

A Cable Kind of Guy?

He often looked a bit too pleased with himself for walking into what was supposed to be a lion’s den and finding Mr. Hannity’s inability to marshal facts as well as he could—while insisting that he, not the Mayor, should be asking the questions—made it a lopsided exchange. It was as if it occurred to Mr. de Blasio that he might have a future on cable TV, where you can do quite well simply playing to your base, with no need to understand people on the other side of the argument as long as your ratings stay high.

That may explain his prolonging a campaign that has lit no spark in the national electorate and offers no promise of doing so. It is as if this is Mr. de Blasio’s version of a cross-country drive after college, getting away from familiar surroundings, discovering worlds and people outside your prior experience and finding you can thrive if not anchored to the reputation that’s marked you back home, for better and worse.

And with taxpayers covering your security costs and campaign contributors with future business before the city bankrolling your travel and expenses, it’s like your parents are providing you with one big free adventure—complete with all the junk food to be found at the state fair—before you have to return home to reality and figure out what you’re going to do now that you’re a grown-up.

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YES. Besides longtime problems on Rikers that led to harsh criticism of a culture that a former Federal prosecutor said stokes violence, its isolation makes it difficult to transport inmates to courthouses and creates a hardship for family members who want to visit them.

NO. A steady rise in shootings in several boroughs this year may be an indication that crime is on the rise and the smaller jails won't be able to house all the violent felons who deserve to be locked up. And who knows whether whoever's Mayor in seven years will favor the plan?